While ordering food as a law firm employee, Jason Finger figured out what would make the task easier: Web menus. He had no idea he was starting an online food delivery revolution.

“If Henry Ford had asked people what they wanted, they would have said a faster horse; they wouldn’t have been able to envision a car,” Jason Finger says. “Remember that most feedback will be negative when you're starting out. People will tell you that the market is too small, that you won’t be able to make a go of it. But markets change, and they could all be wrong in the end.”

Finger took on the almost nonexistent market of automated restaurant takeout and delivery ordering in 1999 when he co-founded SeamlessWeb (now Seamless). Naysayers told him it would never fly, but he kept at it and sold the company, an online portal for restaurant takeout and delivery, in 2006 to ARAMARK for an undisclosed amount. Finger is now actively involved in advising early stage startups.

As for Finger’s seemingly harebrained business idea? Seamless is a company alive and well, on par this year to rake in a reported $100 million.

When you started your first company in college, you were given a cease and desist letter from a competitor?

At the University of Maryland, I started selling jewelry for fraternities and sororities. I had to stop, though, when a competitor told us we weren’t authorized to operate our business. After that, I decided I wanted to be on the sending end of that letter, so I went to law school at NYU and got my J.D./M.B.A.

How did you come up with the idea for SeamlessWeb?

I was working as an associate at a New York law firm and we would work late, so I would collect everyone’s takeout orders simply because I could charge it on my credit card and get 2 percent cash back. I was making about 11 cents per hour doing that [laughing]. Anyway, one Thanksgiving I was about to take orders and couldn’t find restaurants that were open, so I worked with my co-founders to come up with the idea of starting a company with Web-enabled menus.

The whole idea centered on making it easier for companies to enter in food budget restrictions. Employees could then order and the restaurant would charge the company, [eliminating] any need for employee reimbursement.

Once you came up with the idea, did you immediately quit your job at the law firm?

It wasn’t immediate. A few months later, I told a partner at the firm about my idea. He was great; he agreed to be my first client and even invested a little. Over the course of a few months, we raised about $347,000 from 44 separate people. It was a little nuts.

What was it like in the early days?

For the first several years, we were only focused on enterprises, not individual consumers. I would wake up, call law firms in the morning to alert them to the service, call restaurants throughout the day, help with delivery if restaurants didn’t offer it, then come home and work the customer service line—my apartment phone number—until 11 p.m. Sometimes I would stay up all night just in case people called. Eventually, we hired someone to work nights. It was a pretty slow slog.

What challenges did you face starting out?

Too many to mention, but here are two big ones: First, we were onboarding a major investment bank when we accidentally sent a test email to every single employee at the bank—we are talking tens of thousands. I got the call from my engineer at 2 a.m. and thought I was going to be sick. But, thankfully, the bank gave us another chance after we apologized and promised it would never happen again.

Another one was in 2001. Things were going well, we were on a path to profitability, and then everything stopped after 9/11. We had no money coming in and I remember putting payroll on my credit card. We were very close to going out of business.

When did things pick up for you?

Things got better around 2005 when we focused on launching our consumer offering. By then, people were getting more comfortable using personal credit cards online. ARAMARK purchased us soon after that.

What does the future hold for you? Do you see yourself starting another company someday?

I would like to be involved in the startup community/ecosystem. I especially enjoy the stage of idea to pre-revenue to immediately after post-revenue. I think those moments are very exciting in the evolution of a business. That said, I have two kids now and can no longer work 100 hours a week. I think my ideal situation would be to function as an adviser to two or three businesses on a part-time basis, helping them get off the ground. In fact, I'm working towards these goals right now. At the moment, I'm helping to incubate a few businesses and advising budding startups.

Katie Morell is an independent journalist based in San Francisco. She regularly contributes to Hemispheres, USA Today, Consumers Digest, Destination Weddings & Honeymoons, Crain’s Chicago Business and others.